Medical adhesive dressings are used for a variety of medical applications, such as for securing medical devices to skin. Adhesive dressings can provide barrier protection from infectious species to a wound or catheter insertion site. Transparent adhesive dressings are commonly used at a catheter insertion site because visual monitoring of the site can be achieved without removing the dressing. Poor or weak securement of an inserted medical device can increase the risk for potential infiltration of antagonistic microbes which can result in the need for device reinsertion or can lead to complications such as phlebitis and catheter related bloodstream infections (CRBSIs). When a patient experiences a CRBSI, mortality and morbidity rates increase significantly. Because loss of a catheter line or other medical device can be so devastating for the patient, adhesives which have strong adhesion to the skin are often used to secure such devices; these adhesives, however, can be very damaging to skin when removed. Use of a more gentle adhesive can significantly reduce skin damage such as edema, erythema, and skin stripping or tearing. Common gentle adhesives (e.g., silicone-based adhesives), however, typically have poor adhesion to the inserted medical devices and/or tubing.